This compound belongs to the class of organic compounds known as phenoxyacetic acid derivatives. These are compounds containing an anisole where the methane group is linked to an acetic acid or a derivative.
External Descriptors
Not available
1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.
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Application Protocols
Preparation of analytical stock solutions (general guidance)
Weigh under inert atmosphere if possible (argon backfill as per item storage). Dissolve at 1–10 mg/mL in acetonitrile or methanol. For LC–MS, consider 1 mg/mL in ACN, store aliquots at −20 °C to limit hydrolysis.
For aqueous assays, dilute stock into buffer while vortexing; keep final organic content ≤1–2% if biology requires, or as validated.
HPLC/UPLC method development (example starting point; adjust as needed)
Column: C18, 100 × 2.1 mm, 1.7–3 µm; 30 °C.
Mobile phases: A = water + 0.1% formic acid (or ammonium formate pH ~4–6 for MS compatibility); B = acetonitrile.
Gradient: 30% B to 90% B over 8 min; hold 2 min; re-equilibrate.
Flow: 0.3 mL/min; UV detection 230–280 nm; MS ESI+ with selected ion monitoring for parent and acid metabolite.
Hydrolysis stress test (stability-indicating)
Prepare ~100 µg/mL solutions in ACN/H2O (10:90). Adjust to pH 3 (HCl) or pH 10 (Na2CO3). Incubate at 25–40 °C; sample over time for LC analysis to quantify acid formation.
These protocols are generic starting points and must be validated in your laboratory. No medical or clinical applications are implied.
Biological Roles
Scope note
The following describes general, literature-based biological roles of cloquintocet‑mexyl as a research compound in plant/agrochemical science. It is not a therapeutic and is supplied strictly for research use only.
Literature/general description
Classified as an herbicide safener in crop science; in plants it has been reported to modulate detoxification pathways (e.g., induction of glutathione S‑transferases and related Phase II enzymes), thereby altering the selectivity profile of co-applied herbicidal actives. The effects are species- and context-dependent and are investigated in controlled research settings.
Metabolism: undergoes ester hydrolysis to the corresponding carboxylic acid, along with conjugation reactions (e.g., glucose or glutathione conjugates of downstream metabolites) in plant systems; metabolic profiling is commonly performed via LC–MS/MS.
Environmental fate studies examine partitioning (high hydrophobicity implies sorption to organic matter), hydrolysis rate vs pH, and photolysis potential due to the quinoline chromophore.
Experimental considerations
Use well-defined dosing solutions (often in ACN or acetone with low carrier percentage) and appropriate controls to distinguish safener effects from solvent artifacts.
Analytical tracking typically uses multiple reaction monitoring (MRM) transitions of cloquintocet‑mexyl and its acid metabolite; authentic standards for both species improve quantitation.
Consult primary literature and regulatory monographs for detailed biochemical pathways and organism-specific responses.
Buffer Applications
Cloquintocet‑mexyl is a hydrophobic organic ester and is not used as a buffering agent. It has no defined acid/base pair suitable for maintaining pH in aqueous systems under typical laboratory conditions.
Practical note
For aqueous dosing in bioassays, prepare concentrated stocks in miscible organic solvents (e.g., acetonitrile, methanol, DMSO) and dilute into the target buffer with vigorous mixing; keep the final organic content as low as assay tolerates.
If pH-stability studies are required, select standard buffers (phosphate, acetate, borate, carbonate) and monitor for ester hydrolysis over time by LC.
Green Alternatives
While Cloquintocet‑mexyl itself is an active research analyte and not replaceable when specifically required, the choice of solvents and auxiliaries around it can be optimized for greener practice.
Greener solvent choices (literature/general)
Replace DCM/chloroform with ethyl acetate or 2‑MeTHF for extractions and chromatography when selectivity allows.
Prefer acetonitrile or ethanol/methanol over DMF/DMSO when feasible for LC standards and reactions, noting performance and toxicity tradeoffs.
Use heptane/isohexane in place of hexane (lower toxicity) for normal-phase work.
Workup/waste minimization
Design LC methods with higher aqueous content or ethanol modifiers to reduce ACN use; employ UHPLC to cut solvent consumption.
Solid-phase extraction (SPE) can reduce bulk solvent in residue analysis.
Comparative considerations (general)
| Choice | Benefit | Tradeoff |
|---|---|---|
| Ethyl acetate vs DCM | Lower toxicity, biodegradable | Slightly higher bp; different selectivity |
| 2‑MeTHF vs THF | Bio-based, less peroxide-prone | Water miscibility lower; UV cut-off higher |
| Ethanol vs ACN | Renewable, safer | Higher viscosity; different LC selectivity |
Implement solvent recovery (rotary evaporation with cold traps) and segregate halogenated from non-halogenated waste to improve lifecycle metrics.
Pharmaceutical Uses
This product is not intended for pharmaceutical formulation or clinical use.
Research-only context
May be employed as a chemical reference material in analytical laboratories for method development, validation, and stability-indicating assays (e.g., LC/LC–MS) unrelated to human or veterinary therapeutics.
Excipient status and pharmacopeia
Not listed as a pharmacopeial excipient and has no recognized role in drug product formulation.
For any regulated application, obtain approval-grade reference standards and follow applicable GMP/GxP requirements; this listing is for research use only.
Physical Properties
Item-specific specifications
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.
Molecular formula: Not specified for this item; refer to CoA/Spec Sheet.
Literature/general characteristics (no item-specific guarantee)
Physical state: typically a hydrophobic organic solid or viscous oil depending on sample and temperature; low volatility compared to simple solvents (literature/experience).
Solubility profile: sparingly soluble in water; soluble in common organic solvents (acetone, acetonitrile, dichloromethane, ethyl acetate, methanol, ethanol) and in polar aprotics such as DMF/DMSO (literature/reports).
Polarity/lipophilicity: high lipophilicity expected for an aryloxyacetate with a branched alkyl ester and a chloroquinoline ring (literature consensus). LogP values reported in the literature are high (hydrophobic); consult primary sources for exact numbers.
Thermal behavior: esters of this class are generally thermally stable under typical laboratory handling but can undergo hydrolysis under strong acidic/basic conditions or prolonged heating in wet media (general chemistry knowledge).
Spectroscopic notes: UV-active due to quinoline chromophore; typical UV absorbance in the near-UV (200–350 nm) suitable for HPLC-UV detection (literature/generic for quinolines). Exact ε/λmax not specified here.
For authoritative, lot-specific values (MP/BP, density, refractive index, water content, etc.), refer to the CoA/Spec Sheet and SDS.
Quality and Grades
Item-specific quality attributes
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Stabilizers/Inhibitors: Not specified for this item; refer to CoA/Spec Sheet.
Guidance on interpreting grade (general)
For reference-standard or analytical applications (e.g., method validation, residue analysis), look for materials accompanied by detailed CoA parameters: assay (HPLC/GC), identity (NMR/IR/MS), residual solvents, related substances, water content (Karl Fischer), and stability data.
If “analytical standard” or “certified reference material (CRM)” is required, ensure traceability to primary standards and documented uncertainty; this listing does not claim CRM status.
For synthetic use, a standard research grade with high assay and low volatile/trace-metal content is usually sufficient; UV cutoff is relevant only for chromatographic detection and is not specified here.
Implications of storage under argon (item-specific)
Argon-charged packaging suggests sensitivity to oxygen and/or moisture. Maintain inert headspace after opening; consider backfilling with argon or nitrogen, and tightly recap to preserve quality.
Refer to the lot-specific CoA for definitive assay and impurity limits, and contact Technical Support for validation packages (chromatograms, spectra) if needed.
Reaction and Applications
Research applications (non-clinical; literature/general)
Commonly used as a non-therapeutic reference standard in environmental fate, metabolism, and residue-analytical studies for safener/herbicide formulations (research use only).
Analytical method development: calibration curves for LC-UV/LC–MS/MS; extraction recovery studies from plant/soil matrices; hydrolysis kinetics under pH-stress.
Chemical behavior (general chemistry)
Ester functionality: susceptible to base- or acid-catalyzed hydrolysis to the corresponding carboxylic acid; transesterification under alcoholysis with acid/base catalysis.
Aryloxy linkage: typically robust, but can be cleaved under strong nucleophilic or reductive conditions (e.g., harsh hydrogenolysis is generally ineffective; specialized conditions needed).
Quinoline ring: participates in electrophilic substitution at activated positions; N-oxide formation under peracids; metalation adjacent to heteroatom under directed lithiation conditions.
Practical tips
Handle under inert gas (argon/nitrogen) as per item-specific guidance; use dry glassware and solvents for kinetic or stability studies.
For LC/MS: minimize exposure to strong bases/acids in aqueous media; prepare fresh standards or store frozen aliquots in ACN with minimal water content.
If synthesizing related analogs, the aryloxyacetate motif can be constructed via SNAr of a haloquinoline-8-ol derivative followed by O-alkylation and esterification, or via Mitsunobu-type ether formation then acylation (general routes).
Cross-reference
Manufacturer Applications: Not specified in Product Data; typical uses above reflect literature practices for research and analytical workflows.
Reaction Conditions
The following are general, literature-style conditions for chemical manipulations relevant to aryloxyacetate quinoline esters; they are not item-specific specifications.
Ester hydrolysis (to acid)
Base-catalyzed: 0.5–1.0 M NaOH or KOH in MeOH/H2O (1:1 to 4:1), 20–40 °C, 1–6 h; monitor by LC. Quench carefully, acidify to pH ~2, extract with EtOAc.
Acid-catalyzed: conc. HCl or H2SO4 (cat.) in MeOH, 20–50 °C, 2–12 h; may favor methyl ester formation (transesterification) if water content is low.
Transesterification
Fischer: ROH (excess), p‑TsOH (1–5 mol%), 50–80 °C; Dean–Stark or molecular sieves to remove water. Alternatively, base-catalyzed using NaOMe/NaOEt in corresponding alcohol at rt–40 °C.
m‑CPBA (1.1–1.5 eq) in DCM at 0–25 °C, 0.5–2 h; monitor by TLC/LC. Workup with aqueous Na2CO3.
LC analytical conditions (example guidance)
Column: C18, 2.1 × 100 mm, 1.7–3 µm; Mobile phase: water (0.1% formic acid) / acetonitrile gradient to 70–90% ACN over 5–10 min; Detection: UV 230–280 nm and/or ESI–MS in positive mode for quinoline chromophore/ionization.
Actual conditions should be optimized for your substrate, scale, and equipment. Observe inert atmosphere handling to match the item’s storage guidance.
Safety and Handling
Product Data (item-specific)
Storage Conditions: Room temperature; store under argon (argon-charged).
Shipping: Normal.
GHS/Signal word/H-statements/Pictograms: Not specified for this item; refer to SDS.
General safety guidance (not item-specific; defer to SDS for compliance)
Likely hazards for hydrophobic quinoline esters may include skin/eye irritation and environmental toxicity to aquatic life; handle as harmful if swallowed/inhaled and as environmentally hazardous unless SDS indicates otherwise.
PPE: use lab coat, safety glasses or chemical splash goggles, and appropriate gloves (e.g., nitrile). Avoid inhalation of dust/aerosols; work in a fume hood for weighing and solution prep.
Incompatibilities: avoid strong bases and strong acids in the presence of water (risk of ester hydrolysis); strong oxidizers may react with aromatic systems; avoid prolonged exposure to moisture/air to minimize hydrolysis or oxidative discoloration.
First aid overview: in case of skin/eye contact, rinse with water for at least 15 minutes; remove contaminated clothing. If inhaled, move to fresh air. If ingested, rinse mouth; seek medical attention in all cases. Provide SDS to responders.
Spills/Waste: absorb with inert material; collect in halogenated/non-halogenated organic waste per local regulations. Prevent release to drains.
Always consult the product SDS for definitive hazard classification, exposure limits, and emergency measures.
Solvent Selection
Cloquintocet‑mexyl is a hydrophobic aryloxyacetate ester bearing a quinoline chromophore.
Analytical standards: acetonitrile or methanol are preferred for LC (HPLC/UPLC) due to volatility and compatibility with aqueous mobile phases; DMSO/DMF for high-concentration stocks, then dilute into ACN/H2O with vigorous mixing.
Preparative workup or recrystallization: ethyl acetate/hexanes or toluene/MTBE systems often give good handling for hydrophobic esters; optimize empirically.
Stability considerations: avoid prolonged contact with wet protic solvents if hydrolysis is a concern; use dry solvents and inert atmosphere when preparing long-term standards.
Comparison notes (literature/general)
ACN vs MeOH: ACN gives sharper LC peaks with lower backpressure and better UV transparency above ~200 nm; MeOH is greener and less toxic but can change selectivity.
DCM/chloroform vs EtOAc/toluene: chlorinated solvents have excellent solvating power but higher environmental/health burdens; use EtOAc or toluene where feasible.
Confirm solubility and solution stability in your exact matrix; filter standards (0.2 µm PTFE) to protect LC systems.
Storage and Reconstitution
Item-specific storage
Store at room temperature under inert gas (argon-charged), tightly closed. Protect from moisture and prolonged air exposure to limit ester hydrolysis and oxidative discoloration.
Prepare concentrated stock solutions in dry acetonitrile or methanol; for maximum stability, use anhydrous solvent, argon backfill, and amber vials.
For high-concentration needs, DMSO can be used; verify compatibility with downstream assays.
Filter solutions for LC (0.2 µm PTFE) and avoid extended storage in basic aqueous media.
Aliquoting and shelf life
Split into single-use aliquots to minimize headspace and freeze–thaw cycles. For long-term storage of solutions, keep at −20 to −30 °C in dry organic solvent; monitor by LC for degradation.
Stability notes
Avoid strong acids/bases and moisture during storage; hydrolysis yields the corresponding acid. Follow the SDS and CoA for any lot-specific stability or retest dates.
For research use only. Refer to the CoA/Spec Sheet for any missing item-specific parameters.
Structure and Identity
Cloquintocet‑mexyl is a quinoline-based aryloxyacetate ester used widely as a non-therapeutic reference compound and agrochemical safener standard (research use only).
Product Data (item-specific)
CAS: 99607-70-2
PubChem CID: 93528
InChIKey: 49858 (as provided in Product Data)
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
Molecular formula: Not specified for this item; refer to CoA/Spec Sheet.
Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.
Structural features (general/literature description)
Contains a quinoline ring system bearing a chloro substituent (aryl chloride) and a phenoxy/quinolinoxy linkage to an oxyacetic acid ester (aryloxyacetate motif).
Functional groups: aryl chloride, aryl ether (–O–Ar), ester (–CO2R). The ester alkyl group is a branched alkyl (commonly referred to as “mexyl”), yielding a hydrophobic, lipophilic tail.
Stereochemistry: the branched alkyl ester can be chiral; commercial material is typically racemic unless otherwise stated (not specified for this item).
2D structural description (general)
A fused benzopyridine (quinoline) core with a chlorine substituent on the ring; at the 8-position the ring oxygen is linked via –O–CH2–COO– to a branched C7-like alkyl chain (“mexyl”), giving an overall amphiphilic, strongly lipophilic ester.
Synthetic Utility
Although cloquintocet‑mexyl is most often handled as a reference analyte rather than a building block, its functional groups provide defined reactivity that can be exploited in method development and in the preparation of analogs.
Transformations of interest (general chemistry)
Ester hydrolysis: controlled conversion to the corresponding carboxylic acid enables comparative studies of parent vs metabolite. Base-catalyzed (NaOH/MeOH–H2O) or acid-catalyzed (HCl/MeOH) routes are typical.
Transesterification: exchange of the “mexyl” group under acid/base catalysis to map structure–property relationships.
Ether stability: the aryloxy (quinolinoxy) linkage is generally robust; cleavage demands strong conditions (e.g., specialized nucleophiles or high-temperature SNAr on suitably activated substrates).
Quinoline modifications: N-oxidation (m-CPBA), halogen–lithium exchange on appropriately positioned halides, and electrophilic substitutions can furnish labeled or functionalized derivatives for analytical tracers.
Retrosynthetic perspective (general)
Assembly often proceeds from a halo- or hydroxy-quinoline precursor, O-alkylation with bromo/iodoacetate, followed by esterification with a branched alcohol (“mexyl” alcohol). Alternative Mitsunobu coupling of quinolin-8-ol with the alcohol then acylation is also reported for related systems.
Care should be taken to preserve the integrity of the aryloxy linkage during basic hydrolysis; phase-transfer conditions can assist at lower temperatures.
Target Specificity
Not applicable. This product is a small-molecule organic compound, not a biological affinity reagent. No antigen/epitope, species reactivity, clone, or isotype data apply. For biochemical context, see the Biological Roles section.
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